Citation: Ji-Ping Liao, Jiang Li, Wen-Jie Qin, Xiu-Mei Duan, Peng-Fei Wang, Jin-Ying Tian, Xiang Yuan, Pei-Cheng Zhang, Fei Ye, Ya-Nan Yang. Two racemic pairs of benzo bicyclo[3.3.1]/[4.2.1] nonene stilbenoid dimers from Heterosmilax yunnanensis and structural revision of syagrusin A[J]. Chinese Chemical Letters, ;2025, 36(9): 110687. doi: 10.1016/j.cclet.2024.110687 shu

Two racemic pairs of benzo bicyclo[3.3.1]/[4.2.1] nonene stilbenoid dimers from Heterosmilax yunnanensis and structural revision of syagrusin A

Ji-Ping Liao ^{a, 1} ,
Jiang Li ^{a, 1} ,
Wen-Jie Qin ^b ,
Xiu-Mei Duan ^b ,
Peng-Fei Wang ^b ,
Jin-Ying Tian ^a ,
Xiang Yuan ^a ,
Pei-Cheng Zhang ^{a, *,} ,
Fei Ye ^{a, *,} ,
Ya-Nan Yang ^{a, *,}

a.
State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, China
b.
Beijing Zhendong Guangming Pharmaceutical Research Institute, Beijing 100085, China

Received Date: 2 October 2024
Revised Date: 25 November 2024
Accepted Date: 27 November 2024
Available Online: 29 November 2024

Figures(8)

Two racemic pairs of new stilbenoid dimers, (±)-heterosmilaxones A (1) and B (2), with unique 6/6/6and 6/5/7 tricyclic core systems, respectively, were isolated from the rhizomes of Heterosmilax yunnanensis. Their structures were elucidated through comprehensive spectroscopic analyses, quantum chemical calculations and X-ray diffraction crystallography. Compound (+)-1, initially reported as syagrusin Awith a 1,4,4a,9a-tetrahydrofluoren-9-one skeleton, is now revised to a new structure characteristic witha benzo bicyclo[3.3.1] nonene scaffold. And compound 2 bears an unprecedented carbon skeleton withfour continuous chiral centers in the central benzo bicyclo[4.2.1]nonene motif. Biogenetically, both 1 and 2 were proposed to derive from 3,3',4,5,5'-pentahydroxy stilbene and could be generated through keyinverse-electron-demand [4 + 2] and [5 + 2] cycloadditions, respectively. Interestingly, both (±)-1 and(±)-2 showed significant inhibition against α-glucosidase. (±)-1 and its pure enantiomers could modulate protein tyrosine phosphatase-1B (PTP1B) enzyme activities and increased glucose consumption inHepG2 cells in a dose-dependent manner.
- Heterosmilax yunnanensis,
- Stilbenoid dimer,
- Heterosmilaxones A and B,
- Structural revision of syagrusin A,
- Inhibition of α-glucosidase and PTP1B enzyme
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沈阳化工大学材料科学与工程学院沈阳 110142